Heemanjst feitzsche



Patented Dec. 22, 1925.

UNITED STATES 1,566,742 PATENT OFFICE.

HERMANN FRITZSCHE AND PAUL SCHKDELI, BASEL, SWITZERLAND, ASSIGNORS TO THE FIRM SOCIETY OF CHEMICAL INDUSTRY IN BASLE, OF BASEL, SWITZER- LAND.

AROMATIG DERIVATIVE or CYANURICCHLORIDE AND rnocnss non rnonuomo No Drawing.

To all whom it may concern:

Be it knownthat we, HERMANN F mrzsorm and PAUL Sorn'innm, both citizens of the Swiss Confederation, and residing at Basel, Switzerland, have invented new and useful Improvements in Aromatic Derivatives of Uyanuric Chloride and Process for Producing Same, of which the following is a full, clear, and exact specification.

The invention relates to new products which are valuable for the manufacture of dyestuffs or other products.

It has been found that new nucleal condensation products may be obtained by causmg one to two molecular proportions of a-naphthol and two toone molecular proportions of any other. aromatic compound adapted of yielding nucleal condensation products to react in any desired sequence on one molecular proportion of a cyanuric halide.

There are thus" obtained products of the general formula:

wherein A and B stand for any aromatic nuclei, of which one only may be a p-hydroxynaphthalene nucleus. The new products when obtained by acidification of their alkaline solutions, form red to red-violet and brown powders, insoluble in water, dissolving in caustic soda solution with yellow, in concentrated sulfuric acid with red to violet coloration; they are valuable parent mate- .rials for the manufacture of dyestuffs.

Example 1.

93 parts of cyanuric chlori e and 93 parts of aluminim chloride are introduced into 1500 parts of carbon disulfide. ,After 5 minutes 144 parts of a-naphthol are added in small portions and the mixture is stirred for 10-12 hours. The product of reaction is separated from the diluent and treated in the same vessel for 8 hours and near the boil- Application filed March 26, 1925.

Serial No. 18,800.

ing point temperature of the xylene with 1500 parts of the diluent and parts of aluminum chloride. .The product of reaction, which is mostprobably the 2.4-di- 'p-hydroxynaphthyl-6-xylyl 1.3.5-triazine is purified by repeated dissolution in caustic soda solution and precipitation with acids. 00 It forms a red-brown powder dissolving in caustic soda solution with yellow, in concentrated sulfuric acid with red-violet coloration. It corresponds very probably with the formula:

H Example 9.

' 72 parts of a-naphthol, 93 parts of cyanuric trated sulfuric acid with violet coloration and corresponds very probably with the formula:

on N L o \c/ Example 3.

is thus obtained a brown-red powder, dis

solving in caustic soda solution with yellow, in concentrated sulfurlc acid with red coloration, and which is most probably the 2.4-

' di-p-hydroxynaphthyl-6-resorcyl-1.3.5 triazine otthe formula:

Example 4.

39.9 parts of the nucleal condensation product from 1 molecular proportion of cy-v anuric chloride and 2 molecular proportions of oz-naphthol are suspended in 300 arts of tetrachlorethane, 3O partsof fi-na ht c1 and 40 parts of aluminium chloride eing then added. The mixture is heated to 140 C. and

' the diluent distilled off with steam. The

residue is purified as mentioned. in 'the presulfuric acid with violet coloration; .it is I most probably the 2.4-diara-hydroxynaphthyl-G-(i-methoxynaphthy -1.3.5-triazine.

Ewample 6. 50 parts of 2.4-di-para-hydroxynaphthyl- 6-chloro-1.3.5-triazine are prepared according to the directions of Example 1 and suspended in 1000 parts of tetrachlorethane and then heated for 6 hours at 140 C. with 20 parts of'p-cresol and 50 parts of aluminium chloride; The diluent is distilled with steam and the residue purified by repeated dissolution in caustic soda solution and precipitation with acids. The 2.4-di-para-hydroxynaphthyl-ti-para-cresyl-1.3.5-triazine forms a red-brown powder, dissolving in dilute caustic soda solution with yellow, in concentrated sulfuric acid withred-violet coloration; The 2.4-di-para-hydroxynaphthyl-6- anthracene-1.3.5-triazine, prepared in the same manner from 2.4-di-para-hydroxynaphthyl-6-chloro-1.3.5-triazine and anthracene,

forms a red-violet powder,'dissolving in caustic soda solution with yellow, in concentrated sulfuric acid with violet coloration. The two substances of this example correspond probably with the following formulas:

ceding example. The 2.4-di-p-hydroxynaphthyl 6 ,8 hydroxynaphthyl 1.3.5 triazine forms a minimum-red colored powder, dissolving 1n caustic soda solution with yellow,

in concentrated sulfuric acid with violet coloration.

Example 5.

A mixture of 93 arts of aluminium chlo ride and 93' parts 0? cyanuric chloride is introduced into 1500 parts of carbon disulfide. lt tparts of 'a-naphthol are then added in small portions and the whole stirred over night. The 2.4-di-para-hydroxynaphthyl-6- chloro-1.3.5-J;riazine is' filtered, dried and condensed further with 10.00 parts of carbon di-sulfide, 80 parts of S-naphthol-methylether and 50 parts of aluminium chloride. The raw product ispurified by dissolving it several times in caustic soda solution and precipitation with acids. A red-brown powder is obtained, dissolving in caustic soda solution with yellow, in concentrated on and N a t 0.. i it \c/ What we claim is:

1. The herein described process for making cyanuric chloride derivatives, consisting in causing one to two molecular proportions of oz-naphthol and two to one molecular proportions of another aromatic compound adapted of yielding nuclear condensation products to react in any desired sequence on one molecular proportion of.a cyanuric halide.

2. The herein describedprocess for making cyanuric chloride derivatives, consisting in causing two molecular proportions of a-naphthol and one molecular proportion of another aromatic compound adapted of yielding nuclear condensation products to react in any desired sequence on one molecular proportion of a cyanuric'halide.

-3. The herein describedprocess for making cyanuric chloride derivatives, consisting in causin two molecular proportions of a-naphtho and one molecular proportion of another aromatic hydroxy compound adapted of yielding nuclear condensation'prodnets to react in any desired sequence on one molecular pro ort10n ofa cyanuric halide.

4. The hereln described process for making cyanuric chloride derivatives, consisting in causing two molecular proportions of a-naphthol and one molecular proportion of another hydroxy compound of the naphthalene series adapted of yielding nuclear condensation products to react in any desired sequence on one melocular proportion of a cyanur1c hallde.

5. The herein described process for making cyanuric chloride derivatives, consisting in causin two molecular proportions of a-naphtho and one molecular proportion of fi-naphthol to react on one molecular proportion of a cyanuric halide.

6. As new products the new compounds of the general formula:

A m a-d d-n wherein A and B stand for an aromatic nuclei, of which one only may a p-hydroxynaphthalene nucleus, the new products forming, when obtained by acidification of their alkaline solutions, red to red-violet and brown powders, insoluble in' water, dissolving in caustic soda solution with ellow, in concentrated sulfuric acid 'with r to violet coloration. I

7, As new products the new compounds of the general formula:

' 1? it A-d 8-3 V v N v wherein A and" B stand for any aromatic nuclei, of which one only is a p-hydroxynaphthalene nucleus, the new products forming, when obtained by acidification of their 'alkaline solutions red to red-violet and wherein A and B stand for any aromatic nuclei, of which one only isa p-hydroxynaphthalene nucleus and the other another aromatic hydroxy com ound, the new products forming, when 0 tained by acidification of their alkaline solutions, red to redvioletand brown powders; insoluble in water, dissolving in caustic soda solution with yellow, in concentrated sulfuric acid with red to violet coloration.

9. As new products the new compounds of the general formula:

on y

,f 10s A-d d-B \N/ wherein A and B stand for any aromatic nuclei, of which one only-is a p-hydroxynaphthalene nucleus and the other an aromatic hydroxy compound of the naphthalene series, the'new products forming when obtained by acidification of their alkaline solutions, red to brown powders, insoluble in water, dissolving in caustic soda solution with. yellow, in concentrated sulfuric acid with violet coloration.

10. As a new product the new compound wherein A and B stand 'forany aromatic in concentrated sulfuric acid with violet nuclei, of which one only is a, p-hydroxycoloration.

naphthalene nucleus and the other, )the In witness whereof wehavehereunto signed 10 fi-naphthol, the new product forming when our names this 14th day of March, 1925.

obtained by acidification of its zilkaline 'soluv tion a red po'Wder,- insoluble in water, dis- HERMANN FRITZSCHE.

solving in caustic soda solution with yellow, PAUL SCHADELI. 

